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Chemistry

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Also known as: (z)-4-hydroxytamoxifen, Afimoxifene, 68047-06-3, Hydroxytamoxifen, Trans-4-hydroxytamoxifen, 4-monohydroxytamoxifen
Molecular Formula
C26H29NO2
Molecular Weight
387.5  g/mol
InChI Key
TXUZVZSFRXZGTL-QPLCGJKRSA-N
FDA UNII
95K54647BZ

Afimoxifene
Afimoxifene is a tamoxifen metabolite with both estrogenic and anti-estrogenic effects. Afimoxifene has a higher affinity for the estrogen receptor than tamoxifen, and functions as an antagonist in breast cancer cells.
1 2D Structure

Afimoxifene

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
4-[(Z)-1-[4-[2-(dimethylamino)ethoxy]phenyl]-2-phenylbut-1-enyl]phenol
2.1.2 InChI
InChI=1S/C26H29NO2/c1-4-25(20-8-6-5-7-9-20)26(21-10-14-23(28)15-11-21)22-12-16-24(17-13-22)29-19-18-27(2)3/h5-17,28H,4,18-19H2,1-3H3/b26-25-
2.1.3 InChI Key
TXUZVZSFRXZGTL-QPLCGJKRSA-N
2.1.4 Canonical SMILES
CCC(=C(C1=CC=C(C=C1)O)C2=CC=C(C=C2)OCCN(C)C)C3=CC=CC=C3
2.1.5 Isomeric SMILES
CC/C(=C(\C1=CC=C(C=C1)O)/C2=CC=C(C=C2)OCCN(C)C)/C3=CC=CC=C3
2.2 Other Identifiers
2.2.1 UNII
95K54647BZ
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 4'-hydroxytamoxifen

2. 4-(1-(4-(2-(dimethylamino)ethoxy)phenyl)-2-phenylbut-1-enyl)phenol

3. 4-hydroxy-tamoxifen

4. 4-hydroxytamoxifen, (e)-isomer

5. 4-hydroxytamoxifen, (z)-isomer

6. 4-monohydroxytamoxifen

7. 4-oht Hydrotamoxifen

8. 4oh-tamoxifen

9. Afimoxifene

10. Hydroxytamoxifen

11. Ici 79280

12. Monohydroxytamoxifen

13. Para-hydroxytamoxifen

14. Phenol, 4-((1z)-1-(4-(2-(dimethylamino)ethoxy)phenyl)-2-phenyl-1-buten-1-yl)-

15. Phenol, 4-(1-(4-(2-(dimethylamino)ethoxy)phenyl)-2-phenyl-1-butenyl)-

16. Phenol, 4-(1-(4-(2-(dimethylamino)ethoxy)phenyl)-2-phenyl-1-butenyl)-,

17. Tamoxifen Metabolite B

2.3.2 Depositor-Supplied Synonyms

1. (z)-4-hydroxytamoxifen

2. Afimoxifene

3. 68047-06-3

4. Hydroxytamoxifen

5. Trans-4-hydroxytamoxifen

6. 4-monohydroxytamoxifen

7. Tamogel

8. (z)-4-(1-(4-(2-(dimethylamino)ethoxy)phenyl)-2-phenylbut-1-en-1-yl)phenol

9. 68392-35-8

10. Ici 79280

11. 65213-48-1

12. (z)-4-hydroxy Tamoxifen

13. (e/z)-4-hydroxy Tamoxifen

14. Z-4-hydroxytamoxifen

15. C26h29no2

16. Chembl489

17. R-lipoic Acid Potassium Compund

18. Tamoxifen, 4-hydroxy-, (z)-

19. Mls000069742

20. 1077-29-8

21. Chebi:44616

22. (e/z)-4-hydroxytamoxifen

23. 95k54647bz

24. 4-hydroxy Tamoxifen

25. Smr000058939

26. 4-[(1z)-1-{4-[2-(dimethylamino)ethoxy]phenyl}-2-phenylbut-1-en-1-yl]phenol

27. 4-[(z)-1-[4-[2-(dimethylamino)ethoxy]phenyl]-2-phenylbut-1-enyl]phenol

28. 4-hydroxy Tamoxifen-d5

29. 4-oh-tam

30. [3h]4-oht

31. 4-[(1z)-1-[4-[2-(dimethylamino)ethoxy]phenyl]-2-phenyl-1-buten-1-yl]phenol

32. Cis-4-hydroxytamoxifen

33. Sr-01000759243

34. Afimoxifene [usan:inn]

35. Ici 79,280

36. Brn 4910749

37. Unii-17197f0kym

38. Ccris 8580

39. Unii-95k54647bz

40. (z)-4-oht

41. 4-[(1z)-1-{4-[2-(dimethylamino)ethoxy]phenyl}-2-phenyl-1-buten-1-yl]phenol

42. 4-oh Tamoxifen

43. Tamogel (tn)

44. 2bj4

45. Opera_id_600

46. Afimoxifene (usan/inn)

47. Dsstox_cid_2384

48. 4-((1z)-1-(4-(2-(dimethylamino)ethoxy)phenyl)-2-phenyl-1-butenyl)phenol

49. Phenol, 4-(1-(4-(2-(dimethylamino)ethoxy)phenyl)-2-phenyl-1-butenyl)-,

50. Trans-4-(1-(4-(2-(dimethylamino)ethoxy)phenyl)-2-phenyl-1-butenyl)phenol

51. Schembl9189

52. Dsstox_rid_76567

53. Bidd:pxr0104

54. Dsstox_gsid_22384

55. Afimoxifene, Z-isomer

56. Mls001077346

57. Bidd:er0193

58. Cid_449459

59. Dtxsid7022384

60. Bdbm20608

61. 17197f0kym

62. Hms2231f20

63. Zinc902197

64. Ex-a4661

65. Tox21_200943

66. 4-[1-[4-[2-(dimethylamino)ethoxy]phenyl]-2-phenyl-1-butenyl]phenol

67. Hsci1_000353

68. Hy-16950a

69. Ici-79280

70. Mfcd00278780

71. Mfcd00468090

72. S8956

73. (z)-4-hydroxytamoxifen (z-4-oht)

74. 4-{1-[4-(2-dimethylamino-ethoxy)-phenyl]-2-phenyl-but-1-enyl}-phenol

75. Akos016010361

76. Db04468

77. Phenol, 4-((1z)-1-(4-(2-(dimethylamino)ethoxy)phenyl)-2-phenyl-1-butenyl)-

78. Phenol, 4-(1-(4-(2-(dimethylamino)ethoxy)phenyl)-2-phenyl-1-butenyl)-, (z)-

79. Ncgc00164399-01

80. Ncgc00164399-02

81. Ncgc00258497-01

82. (z)-4-hydroxytamoxifen, >=98% Z Isomer

83. Cas-68047-06-3

84. Cs-0003592

85. C05011

86. D06551

87. 392h358

88. A904472

89. Q4689254

90. Sr-01000759243-3

91. Sr-01000759243-5

92. Brd-k04210847-001-01-1

93. 4-(1-[4-(dimethylaminoethoxy)phenyl]-2-phenyl-1-butenyl)phenol

94. (z)-4-(1-(4-(2-(dimethylamino)ethoxy)phenyl)-2-phenylbut-1-enyl)phenol

95. 4-(1-(4-(2-(dimethylamino)ethoxy)phenyl)-2-phenylbut-1-en-1-yl)phenol

96. 4-hydroxytamoxifen ??(1/2)70% Z Isomer (remainder Primarily E-isomer)

97. 4-[(1z)-1-[4-[2-(dimethylamino)ethoxy]phenyl]-2-phenyl-1-buten-1-yl]-phenol

98. 4-{(1z)-1-[4-(2-dimethylamino-ethoxy)-phenyl]-2-phenyl-but-1-enyl}-phenol

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 387.5 g/mol
Molecular Formula C26H29NO2
XLogP36.8
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count8
Exact Mass387.219829168 g/mol
Monoisotopic Mass387.219829168 g/mol
Topological Polar Surface Area32.7 Ų
Heavy Atom Count29
Formal Charge0
Complexity493
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

For the potential treatment of menstrual-cycle related mastalgia, fibrocystic breast disease, breast disease, gynecomastia and Keloid scarring.


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Antineoplastic Agents

Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)


Selective Estrogen Receptor Modulators

A structurally diverse group of compounds distinguished from ESTROGENS by their ability to bind and activate ESTROGEN RECEPTORS but act as either an agonist or antagonist depending on the tissue type and hormonal milieu. They are classified as either first generation because they demonstrate estrogen agonist properties in the ENDOMETRIUM or second generation based on their patterns of tissue specificity. (Horm Res 1997;48:155-63) (See all compounds classified as Selective Estrogen Receptor Modulators.)


Estrogen Antagonists

Compounds which inhibit or antagonize the action or biosynthesis of estrogenic compounds. (See all compounds classified as Estrogen Antagonists.)


5.2 Absorption, Distribution and Excretion

Absorption

Absorbed following topical application.


5.3 Metabolism/Metabolites

4-Hydroxytamoxifen has known human metabolites that include 3,4-Dihydroxy-Tamoxifen, Endoxifen, Tamoxifen 4-O-glucuronide, and Tamoxifen 4-O-sulfate.

4-Hydroxytamoxifen is a known human metabolite of tamoxifen.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560


5.4 Mechanism of Action

Afimoxifene binds to estrogen receptors (ER), inducing a conformational change in the receptor. This results in a blockage or change in the expression of estrogen dependent genes.


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Afimoxifene manufacturers, exporters & distributors 1

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PharmaCompass offers a list of Afimoxifene API manufacturers, exporters & distributors, which can be sorted by GMP, USDMF, JDMF, KDMF, CEP (COS), WC, Price,and more, enabling you to easily find the right Afimoxifene manufacturer or Afimoxifene supplier for your needs.

Send us enquiries for free, and we will assist you in establishing a direct connection with your preferred Afimoxifene manufacturer or Afimoxifene supplier.

PharmaCompass also assists you with knowing the Afimoxifene API Price utilized in the formulation of products. Afimoxifene API Price is not always fixed or binding as the Afimoxifene Price is obtained through a variety of data sources. The Afimoxifene Price can also vary due to multiple factors, including market conditions, regulatory modifications, or negotiated pricing deals.

API | Excipient name

Afimoxifene

Synonyms

(z)-4-hydroxytamoxifen, 68047-06-3, Hydroxytamoxifen, Trans-4-hydroxytamoxifen, 4-monohydroxytamoxifen, Tamogel

Cas Number

68047-06-3

Unique Ingredient Identifier (UNII)

95K54647BZ

About Afimoxifene

Afimoxifene is a tamoxifen metabolite with both estrogenic and anti-estrogenic effects. Afimoxifene has a higher affinity for the estrogen receptor than tamoxifen, and functions as an antagonist in breast cancer cells.

Afimoxifene Manufacturers

A Afimoxifene manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Afimoxifene, including repackagers and relabelers. The FDA regulates Afimoxifene manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Afimoxifene API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

Afimoxifene Suppliers

A Afimoxifene supplier is an individual or a company that provides Afimoxifene active pharmaceutical ingredient (API) or Afimoxifene finished formulations upon request. The Afimoxifene suppliers may include Afimoxifene API manufacturers, exporters, distributors and traders.

Afimoxifene GMP

Afimoxifene Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Afimoxifene GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Afimoxifene GMP manufacturer or Afimoxifene GMP API supplier for your needs.

Afimoxifene CoA

A Afimoxifene CoA (Certificate of Analysis) is a formal document that attests to Afimoxifene's compliance with Afimoxifene specifications and serves as a tool for batch-level quality control.

Afimoxifene CoA mostly includes findings from lab analyses of a specific batch. For each Afimoxifene CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Afimoxifene may be tested according to a variety of international standards, such as European Pharmacopoeia (Afimoxifene EP), Afimoxifene JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Afimoxifene USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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